I recently talked about the free trip we did to Latin America and I have another free trip coming up. But what I want to emphasize is that anyone can get a free trip, they just have to know what they’re doing and how to properly compare deals. Nearly every trip can be filled with free travel with these few steps.
1) Pick The Destination
My tips aren’t so much for picking the destination as they are getting there. But if you’re interested in some of my travel recommendations check out:
There are so many places I’d recommend in this world from Sri Lanka to Italy, that at the end of the day it’s about whatever moves you.
I will say that Google Images is a great place for me to start. For example, you type in “Poland” and browse images, you’ll see a number of pictures of the old capital “Krakow”. Krakow is awesome, but basically everyone in Poland will tell you “Krakow is the most beautiful city in Poland”.
Part of the way that google works is that it puts pictures that get shared around the web a lot at the top of the search results. So in theory beautiful pictures float to the top.
But what I like is that I can see what kind of place it is. I basically look for natural beauty, a beautiful city, or cultural beauty. While cultural beauty isn’t just in pictures, it can be hospitality and what not, but it can be in pictures too. For example, the traditional dress of the people living in the mountains of Peru is telling as to how different that culture is. Same with the traditional dress in India, Bali, the Middle East, and so many places around the world. You can see the culture in foods, dress, homes, etc…
So sometimes I google image search and then look at the name of the places that really catch my attention. In fact, I was looking at Mozambique today to see what showed up.
Anyone else have tips for picking a destination?
Anyways, I put this first because a deal is a great thing, but you should only chase a deal if it’s someplace you want to go. Chase your dreams not deals. But I like to keep a list of my dream destinations so I know when a deal pops up, I’m going because the two align.
2) Find The Cheapest Miles
The best resource I have for that is a partially complete series for “Cheapest Miles To ___”. Click here to check out the series.
So far, I have:
- Cheapest Miles to Hawaii
- Cheapest Miles to Europe
- Cheapest Miles to East Asia
- Cheapest Miles to the Caribbean
The basics would be that you should simply look up what the cheapest flight would be in miles.
3) Find Best Best Credit Card For Those Miles
This is where you’ve got to combine the knowledge of the cheapest miles to the best credit card bonus.
Sometimes a flight with a particular miles program can be super cheap, and impossible to earn. Or the earning are just half as good.
A great example would be Virgin America Elevate miles which have incredible prices (like New York to Germany for 12,000 miles), but you earn miles very slowly. For example, the transfer from American Express is 2:1. It would take 24,000 Amex points to get 12,000 Elevate miles.
Try to think of which card gives the most flights.
A card that gives 25,000 miles but gives a roundtrip to Europe, could be of more value to you than a card that gives 50,000 miles and doesn’t quite give enough miles for a roundtrip. Miles are all relative. Relative to need, relative to what they get you, and to how you earn them.
4) Check Out Award Availability
But before you go signing up for a new card, why not check to make sure there are plenty of flights. If you’re not completely new to this, you know that you can use your miles for any of that airline’s partners in the “alliance” they have.
But, sometimes award availability is really tight for certain routes. Like using United miles to get to Bora Bora is near impossible. Or sometimes flights to South America can be completely hit/miss for award availability. So on and so on.
Therefore you should go ahead and check out the availability for the miles you want to use. Luckily I have a chart that lets you know how to search for flights for each partner.
Check out:
This chart will give you all the info you need for finding specific awards. But if you’re completely unsure just start looking for flights to your destination with the site that shows the most partners, or is easy to use.
I think United.com is really easy to use. You just go to the homepage, pick the flight details and before hitting search, you check “award travel”.
5) Find The Best Hotels
Many great tools popping up for searching for the best hotel awards (which is still relative).
Award Mapper, and Hotel Hustle. Yes, I have hotel maps too, but I see them more useful for someone who has miles and are looking for specific awards. These maps compare different hotel award rates.
Hotel Hustle is a brand new tool that is especially neat because it shows award availability for specific dates in a specific city.
Award Mapper can give a large view of a country or area and all the award prices. I’ve found that a few of the hotel prices are slightly behind the latest devaluation, so you can still check with the hotel website or Hotel Hustle. But the point is that it gives an idea of what miles to use.
I personally can be picky about my location for certain places. Like in Vienna, I want to be in the ring. So I find the main attractions, or the main square of a city (google or wiki) and then compare that on a map with the hotels. I often double check in google maps.
6) Earning Hotel Points
Once you’ve picked a hotel, figure out a way to earn points. Personally, I think IHG points can be earned cheaply via promotions and paid stays. Check out the newest promotion IHG’s Set Your Sights.
Club Carlson sometimes has good hotel promotions, and the credit card makes award stays twice as good because it gives a sort of buy one get one free on awards. Also, the credit card gives 6 points per dollar on everything… which can be really nice.
Hilton points can be earned relatively cheaply via the Surpass Card, which earns 5 points per dollar at drug stores.
When it comes to “free nights” like the Hyatt, Hilton reserve, and Fairmont card give, you’re better off using points than free nights at cheap hotels. Don’t use your free nights at low category hotels, or you should have just gotten a card that gave points.
Also, if you’re looking for other ways to get free nights, check out the Complete Guide to Best Rate Guarantees.
Conclusion
There’s no one way of doing things, and there are many other promotions that come around… but this is a typical way of doing things. Finding the cheapest route, earning the miles, then trying to pick hotels on the cheap. That’s basically the miles and points game in a nutshell.
Hi Drew,
Your posts are wonderful. I have a question on ANA surcharges. I know if I am using ANA miles to fly United domestic there would be no surcharges, but how about flying United on transpacific route, like PEK-ORD-PEK or PVG-SFO-PVG? Thank you very much!
Lee
Great six-step guide. That really covers the brunt of it – thank you. I really like the suggestion to use Google Images. I never thought about doing so to pick a destination, but I think that could be a fun way to go about it.
From a grammatical perspective is it really “cheapest” miles to Europe? Or is it “fewest” miles?
If all of my miles and points were earned naturally with no extra effort or cost on my part, say through a job that required me to travel constantly, then I’d agree with you on “fewest”.
But I generally look at my accrual of miles as more of an investment, especially when doing things like reselling or taking advantage of a promo almost solely for the miles or points. So in my case, “cheapest” makes sense because my goal is to acquire the miles or points I need with as small of an investment as possible.
Great article!
Just to clarify, the Hilton Amex Surpass card has these spending multipliers:
Earn 6X Hilton HHonors Bonus Points for each dollar of eligible purchases on your Card:
at U.S. restaurants
at U.S. supermarkets
at U.S. gas stations
I’ve pursued the reverse path. I wait for the best credit card offers and collect whatever miles come with them before I choose my destination. In this way, I’ve gotten the highest offers (e.g. 100k BA, Amex Plat, Citi AA) which affords me the capacity to select premium cabins, and since I’m diversifying my mile currencies, I’m always able to find availability to whatever destination I’m interested in.
I agree with Stannis. The trouble with picking a destination first is that you may discover few if any viable flight and hotel options that can be redeemed with points or miles and you may end up chasing points that offer poor return. The better path forward is ‘investing’ in a flexible point currency like ultimate rewards then creating a short list of desirable destinations based on where UR’S transfer partners offer the best value. There are so many great destinations you don’t need to pigeon-hole yourself to one and add credit cards to your wallet that you won’t reap benefits from for subsequent trips.
Hi Drew from the-for-example-typed country 😉
Is there any way to benefit from signing up to IHG Rewards? Afaik it is needed to join the Set Your Sights offer and I am thinking on earning some points by registration. Any ideas?
Matt
Thanks, just the other day I was wondering how you approach planning a free trip. I would like to see more information on earning hotel points. I never travel for work, so I might spend 15 nights a year in hotels or so. Does this mean I should focus on credit card sign-up bonuses and transfers from Amex/UR primarily? The whole finding a destination and getting fights on miles isn’t a problem, but I still find myself paying for hotels often.
*flights